Family Weekend in Boston

Boston, Massachusetts, is a great city to explore as a family, with its blend of American history, beautiful parks, and delicious food. Our recent weekend getaway to Boston was filled with family-friendly activities that both the adults and the kids enjoyed. Here’s a rundown of our family weekend in Boston.

Family Weekend in Boston


Day 1: Road Trip from NYC to Boston

We started our family adventure with a four-hour road trip from NYC to Boston. We had plenty of time to chat, play car games, and enjoy the scenery. It was a nice way to ease into the weekend. We kept things simple by each packing clothes in our own hanging packing cube, and stayed at a local Airbnb.

Here are a few of our highlights from Day 1:

Lunch at Black Sheep Bagel Cafe
We started in Cambridge, and headed to Black Sheep Bagel Cafe for a quick lunch. Emily ordered lox, cream cheese, tomato and capers on her bagel, and I can’t stop thinking about my bagel with jalapeño cream cheese, date jam, and egg – the combo was delicious! Our girls shared a more simple plain bagel with strawberry cream cheese. Everyone was happy! (56 John F. Kennedy Street, Cambridge, MA 02138)

Walking Tour of Harvard University
After lunch, we took a stroll around Harvard University’s beautiful campus. Our girls kept busy doing cartwheels on the lawns and searching for colorful leaves in a little scavenger hunt. We also spent some time browsing the Harvard Bookstore, which has a wonderful selection of books for adults and kids! (1256 Massachusetts Avenue, Cambridge, MA 02138)

Sweet Treat at Mike’s Pastry
We also stopped by Mike’s Pastry (it was highly recommended to us on IG!). They’re famous for cannolis, and we tried the peanut butter one along with a classic plain ricotta with chocolate chips, and also a brownie and a classic whoopie pie. It’s a nice little treat spot for families wanting a taste of different Boston desserts and you can eat in the nearby square. (300 Hanover Street, Boston, MA 02113)


Day 2: Exploring Boston’s Iconic Sites

We stayed in an Airbnb in Sommerville, MA and then used Boston’s subway system to get around with the kids, without worrying about finding parking (we got a parking ticket our first afternoon and resolved to NOT to repeat our mistake). Bonus: kids under age 11 ride FREE on the subway!

Here are a few of our highlights from Day 2:

Morning at Boston Common
We started the morning in Boston Common. We grabbed coffee, and our girls enjoyed the Tadpole Playground. The Make Way for Ducklings statues were a big hit – we have the “Make Way for Ducklings” book at home! We also passed Cheers, the Boston pub that inspired the fictional bar in the NBC sitcom.

Midday Freedom Trail Walk
Walking The Freedom Trail is a great way to experience Boston’s history. It’s a 2.5 mile trail that connects 16 nationally significant historic sites, like the Massachusetts State House and Faneuil Hall. The girls loved following the “Red Brick Path”. We also stopped at a playground near City Hall. The tall slides and unique climbing structures were a fun break for the kids.

Lunch at Pauli’s
For lunch, we picked up sandwiches at Pauli’s. Emily opted for an iconic lobster roll, I ordered a Philly cheesesteak (wrong city lol!), and the girls had turkey and cheese on a hero. We headed over to Rose Kennedy Park to eat. It’s a a lovely green space for a picnic. (65 Salem Street, Boston, MA 02113)

Lunch at Pauli's

Afternoon Treat at Bova’s Bakery
After lunch, we stopped at Bova’s Bakery, open 24/7 and full of tasty treats. From Boston cream pie to apple pie, brownies, and cookies, we filled a small bakery box with treats. We ordered at the counter, and then headed to a park and sat by the Paul Revere Statue to eat! We watched several tour groups walk by and got to eavesdrop on the passing tips from the tour guides! (134 Salem Street, Boston, MA 02113)

Boston Duck Boat Tour
One of the highlights of our trip was the Boston Duck Boat Tour, an experience that combines history with adventure! Originally designed for World War II, these amphibious vehicles were meant to carry troops and supplies between water and land. Today, they offer a unique way to see Boston. We started on land, passing sites like the State House and Beacon Hill, and then the Duck Boat drove right into the Charles River for scenic views of the Boston skyline. The captain even let me steer the duck for a bit!

Dinner at Quincy Market
We ended the day at Quincy Market, where everyone found something they liked from the food stalls. Emily and I ordered chowder in bread bowls, and our girls shared a bowl of bacon macaroni and cheese. There’s plenty of seating, and the wide variety of food options makes it a good meal choice for families.


Day 3: Science and More in Boston

For our last day, we started with breakfast at a diner and then headed to one more destination.

Here are a few of our highlights from Day 3:

Breakfast at The Neighborhood Restaurant
The Neighborhood Restaurant had a fun breakfast spread with lots of different options. We ordered pancakes and omelettes with sausage, bacon, home fries, and toast, and the breakfast entrées were served with our choice of Cream of Wheat or freshly baked apple. It was a delicious way to start the day. (25 Bow Street, Somerville, MA 02143)

Museum of Science
Our final stop was the Museum of Science, which is part of the ASTC Passport Program, so we were able to get 4 free tickets with our New York Hall of Science membership — a huge bonus! The museum offers interactive exhibits and hands-on displays, and it was a nice mix of learning and fun for the whole family! (1 Science Park, Boston, MA 02114)


Final Thoughts on a Family Weekend in Boston

Boston offers a variety of family-friendly experiences, dining options, and historic sites that make for a fun and educational trip. Whether you’re there for a weekend or a longer stay, it’s a great city to explore!


Tips for Planning Your Family Trip to Boston:

  • Use Public Transport: Boston’s subway system is easy to navigate, and kids under age 11 ride free!
  • Pack for Comfort: Boston is a walkable city, so comfortable shoes and layers are a good idea.
  • Check Reciprocal Museum Memberships: If you have a local museum membership, you may also get free or reduced entry to museums in Boston, which can be a great money-saver.

Ready to plan your own family weekend in Boston? We hope these highlights and tips help make it a trip filled with history, local flavors, and fun memories. Let the adventure begin!

Thanks for pinning: Family Weekend in Boston

If you liked this, you might also like:

Hi, I'm Tidy Dad!

Tyler Moore is the creator of the “Tidy Dad” Instagram, TikTok, and website. A public school teacher in New York City, husband, and father of three young daughters, he has been featured on Good Morning America and in The Washington Post, The New York Times, New York Post, Better Homes & Gardens Secrets of Getting Organized magazine, Apartment Therapy, and many podcasts including HGTV and Minimalist Moms. During the school year, he lives with his wife, Emily, a pediatric occupational therapist, and three daughters in Queens, New York. In the summer, they spend as much time as possible in their small but tidy cottage in the Poconos.

November 9, 2024

Family Weekend in Boston

Family Weekend in Boston

Boston, Massachusetts, is a great city to explore as a family, with its blend of American history, beautiful parks, and delicious food. Our recent weekend getaway to Boston was filled with family-friendly activities that both the adults and the kids enjoyed. Here’s a rundown of our family weekend in Boston.

Family Weekend in Boston


Day 1: Road Trip from NYC to Boston

We started our family adventure with a four-hour road trip from NYC to Boston. We had plenty of time to chat, play car games, and enjoy the scenery. It was a nice way to ease into the weekend. We kept things simple by each packing clothes in our own hanging packing cube, and stayed at a local Airbnb.

Here are a few of our highlights from Day 1:

Lunch at Black Sheep Bagel Cafe
We started in Cambridge, and headed to Black Sheep Bagel Cafe for a quick lunch. Emily ordered lox, cream cheese, tomato and capers on her bagel, and I can’t stop thinking about my bagel with jalapeño cream cheese, date jam, and egg – the combo was delicious! Our girls shared a more simple plain bagel with strawberry cream cheese. Everyone was happy! (56 John F. Kennedy Street, Cambridge, MA 02138)

Walking Tour of Harvard University
After lunch, we took a stroll around Harvard University’s beautiful campus. Our girls kept busy doing cartwheels on the lawns and searching for colorful leaves in a little scavenger hunt. We also spent some time browsing the Harvard Bookstore, which has a wonderful selection of books for adults and kids! (1256 Massachusetts Avenue, Cambridge, MA 02138)

Sweet Treat at Mike’s Pastry
We also stopped by Mike’s Pastry (it was highly recommended to us on IG!). They’re famous for cannolis, and we tried the peanut butter one along with a classic plain ricotta with chocolate chips, and also a brownie and a classic whoopie pie. It’s a nice little treat spot for families wanting a taste of different Boston desserts and you can eat in the nearby square. (300 Hanover Street, Boston, MA 02113)


Day 2: Exploring Boston’s Iconic Sites

We stayed in an Airbnb in Sommerville, MA and then used Boston’s subway system to get around with the kids, without worrying about finding parking (we got a parking ticket our first afternoon and resolved to NOT to repeat our mistake). Bonus: kids under age 11 ride FREE on the subway!

Here are a few of our highlights from Day 2:

Morning at Boston Common
We started the morning in Boston Common. We grabbed coffee, and our girls enjoyed the Tadpole Playground. The Make Way for Ducklings statues were a big hit – we have the “Make Way for Ducklings” book at home! We also passed Cheers, the Boston pub that inspired the fictional bar in the NBC sitcom.

Midday Freedom Trail Walk
Walking The Freedom Trail is a great way to experience Boston’s history. It’s a 2.5 mile trail that connects 16 nationally significant historic sites, like the Massachusetts State House and Faneuil Hall. The girls loved following the “Red Brick Path”. We also stopped at a playground near City Hall. The tall slides and unique climbing structures were a fun break for the kids.

Lunch at Pauli’s
For lunch, we picked up sandwiches at Pauli’s. Emily opted for an iconic lobster roll, I ordered a Philly cheesesteak (wrong city lol!), and the girls had turkey and cheese on a hero. We headed over to Rose Kennedy Park to eat. It’s a a lovely green space for a picnic. (65 Salem Street, Boston, MA 02113)

Lunch at Pauli's

Afternoon Treat at Bova’s Bakery
After lunch, we stopped at Bova’s Bakery, open 24/7 and full of tasty treats. From Boston cream pie to apple pie, brownies, and cookies, we filled a small bakery box with treats. We ordered at the counter, and then headed to a park and sat by the Paul Revere Statue to eat! We watched several tour groups walk by and got to eavesdrop on the passing tips from the tour guides! (134 Salem Street, Boston, MA 02113)

Boston Duck Boat Tour
One of the highlights of our trip was the Boston Duck Boat Tour, an experience that combines history with adventure! Originally designed for World War II, these amphibious vehicles were meant to carry troops and supplies between water and land. Today, they offer a unique way to see Boston. We started on land, passing sites like the State House and Beacon Hill, and then the Duck Boat drove right into the Charles River for scenic views of the Boston skyline. The captain even let me steer the duck for a bit!

Dinner at Quincy Market
We ended the day at Quincy Market, where everyone found something they liked from the food stalls. Emily and I ordered chowder in bread bowls, and our girls shared a bowl of bacon macaroni and cheese. There’s plenty of seating, and the wide variety of food options makes it a good meal choice for families.


Day 3: Science and More in Boston

For our last day, we started with breakfast at a diner and then headed to one more destination.

Here are a few of our highlights from Day 3:

Breakfast at The Neighborhood Restaurant
The Neighborhood Restaurant had a fun breakfast spread with lots of different options. We ordered pancakes and omelettes with sausage, bacon, home fries, and toast, and the breakfast entrées were served with our choice of Cream of Wheat or freshly baked apple. It was a delicious way to start the day. (25 Bow Street, Somerville, MA 02143)

Museum of Science
Our final stop was the Museum of Science, which is part of the ASTC Passport Program, so we were able to get 4 free tickets with our New York Hall of Science membership — a huge bonus! The museum offers interactive exhibits and hands-on displays, and it was a nice mix of learning and fun for the whole family! (1 Science Park, Boston, MA 02114)


Final Thoughts on a Family Weekend in Boston

Boston offers a variety of family-friendly experiences, dining options, and historic sites that make for a fun and educational trip. Whether you’re there for a weekend or a longer stay, it’s a great city to explore!


Tips for Planning Your Family Trip to Boston:

  • Use Public Transport: Boston’s subway system is easy to navigate, and kids under age 11 ride free!
  • Pack for Comfort: Boston is a walkable city, so comfortable shoes and layers are a good idea.
  • Check Reciprocal Museum Memberships: If you have a local museum membership, you may also get free or reduced entry to museums in Boston, which can be a great money-saver.

Ready to plan your own family weekend in Boston? We hope these highlights and tips help make it a trip filled with history, local flavors, and fun memories. Let the adventure begin!

Thanks for pinning: Family Weekend in Boston

If you liked this, you might also like:

November 9, 2024

Family Weekend in Boston

Hi, I'm Tidy Dad!

Tyler Moore is the creator of the “Tidy Dad” Instagram, TikTok, and website. A public school teacher in New York City, husband, and father of three young daughters, he has been featured on Good Morning America and in The Washington Post, The New York Times, New York Post, Better Homes & Gardens Secrets of Getting Organized magazine, Apartment Therapy, and many podcasts including HGTV and Minimalist Moms. During the school year, he lives with his wife, Emily, a pediatric occupational therapist, and three daughters in Queens, New York. In the summer, they spend as much time as possible in their small but tidy cottage in the Poconos.

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